Methylene C(sp3)−H Arylation Enables the Stereoselective Synthesis and Structure Revision of Indidene Natural Products
Dr. Anton Kudashev
University of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056 Basel, Switzerland
These authors contributed equally to this work.
Search for more papers by this authorDr. Stefania Vergura
University of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056 Basel, Switzerland
These authors contributed equally to this work.
Search for more papers by this authorDr. Marco Zuccarello
University of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056 Basel, Switzerland
Search for more papers by this authorProf. Dr. Thomas Bürgi
University of Geneva, Department of Physical Chemistry, 30 Quai Ernest-Ansermet, 1211 Geneva 4, Switzerland
Search for more papers by this authorCorresponding Author
Prof. Dr. Olivier Baudoin
University of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056 Basel, Switzerland
Search for more papers by this authorDr. Anton Kudashev
University of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056 Basel, Switzerland
These authors contributed equally to this work.
Search for more papers by this authorDr. Stefania Vergura
University of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056 Basel, Switzerland
These authors contributed equally to this work.
Search for more papers by this authorDr. Marco Zuccarello
University of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056 Basel, Switzerland
Search for more papers by this authorProf. Dr. Thomas Bürgi
University of Geneva, Department of Physical Chemistry, 30 Quai Ernest-Ansermet, 1211 Geneva 4, Switzerland
Search for more papers by this authorCorresponding Author
Prof. Dr. Olivier Baudoin
University of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056 Basel, Switzerland
Search for more papers by this authorAbstract
The divergent synthesis of two indane polyketides of the indidene family, namely (±)-indidene A (11 steps, 1.7 %) and (+)-indidene C (13 steps, 1.3 %), is reported. The synthesis of the trans-configured common indane intermediate was enabled by palladium(0)-catalyzed methylene C(sp3)−H arylation, which was performed in both racemic and enantioselective (e.r. 99 : 1) modes. Further elaboration of this common intermediate by nickel-catalyzed dehydrogenative coupling allowed the rapid installation of the aroyl moiety of (±)-indidene A. In parallel, the biphenyl system of (±)- and (+)-indidene C was constructed by Suzuki–Miyaura coupling. These investigations led us to revise the structures of indidenes B and C.
Open Research
Data Availability Statement
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